Compound 1d

(R)-2-((3-((3R,5R,7R)-adamantan-1-yl)-2-hydroxy-5-methylbenzyl)amino)-N,N,3-trimethylbutanamide

From: Catalytic enantioselective addition of organoboron reagents to fluoroketones controlled by electrostatic interactions

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Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

The title compound was synthesized analogous to 1a except the imine formation was performed at 30 °C for 18 h. Imine reduction required 13 equiv. of NaBH4, and the product was purified by silica gel chromatography (24 mm diameter column slurry packed with ~15 g of silica gel and eluted with 1:3 hexanes:diethyl ether) affording 1d (189.1 mg, 0.47 mmol, 74% yield over 3 steps) as white foam. IR (CHCl3): 3544 (br, w), 1641 (w), 1452 (w), 1296 (w), 1228 (w), 1157 (s), 1011 (w), 994 (w), 941 (w), 912 (w), 761 (w), 731 (m) cm–1; 1H NMR (400 MHz, CDCl3): δ 10.71 (1H, s), 6.94 (1H, s), 6.60 (1H, s), 4.03 (1H, d, J = 13.5 Hz), 3.41 (1H, d, J = 13.5 Hz), 3.28 (1H, d, J = 5.9 Hz), 3.04 (3H, s), 2.90 (3H, s), 2.62 (1H, s), 2.22 (3H, s), 2.20–2.11 (6H, m), 2.06 (3H, s), 1.85–1.73 (7H, m), 0.95 (6H, t, J = 6.6 Hz); 13C NMR (100 MHz, CDCl3): δ 173.5, 154.7, 137.0, 127.2, 127.1, 126.6, 122.7, 61.1, 51.5, 40.4, 37.2, 37.0, 36.7, 35.7, 31.2, 29.2, 20.8, 20.0, 17.9; HRMS Calcd for C25H39N2O2[M+H]+: 399.3011; Found: 399.3009; [α]22.0D = +31.962 (c = 0.98, CHCl3)

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